Insights | Sales

Recapping The 2018 Bowery Capital Sales Summit & Themes for The Year Ahead

July 01, 2019

Bowery Capital Sales SummitLast Thursday, December 6th, we hosted the Annual Bowery Capital Sales Summit at Rise New York, and it was a blast. We brought together sales leaders from the NYC SaaS ecosystem and beyond, and wisdom was flowing from start to finish. This post will recap the major themes on the day that we learned from leaders at the likes of Bitly, CloserIQ, Honey, InsightSquared, Klara, SalesLoft, Slack, Stripe, and Yext.

The Best Demand Gen Strategies from 2018 by Wendi Sturgis (Chief Client Officer, Yext)

Wendi kicked off the Sales Summit strong by discussing the best learnings from Yext this year when it comes to building your demand gen engine. Our biggest takeaway from her talk? You should really think about your “Party of 5” and how they all affect demand gen strategies together, as it’s an integrated effort, not just a traditional marketing effort. What is the Party of 5? This would be the activity around AE Outbound, upsells, marketing, partnerships, and SDR efforts.

Within this 5-pronged effort, there are some additional learning lessons that Wendi highlighted:

1. “Challenger Selling” is efficient when it comes to boosting your demand gen strategy, as it’s more noticeable and sticks out from the noise.

2. Website optimization, while a seemingly small thing, makes a huge difference. Yext reduced the number of inbound fields required to submit information from 9 to 6, and experienced a 200% increase in leads (with no additional traffic).

3. Efficient partnerships & strategic alliances led to deals initiated through those partnerships closing 25% faster than other channels.

4. Finally, my favorite piece of advice from Wendi: start holding a customer conference earlier than you think you should. What starts off as a dozen like-minded professionals in a room can quickly grow to thousands of diverse professionals collaborating together, all in the name of your product bringing them together. How could this not be my favorite tip at our humble conference of 100+ SaaS sales leaders in NYC?

Thanks for bringing good energy to start the Sales Summit, Wendi!

3 Lessons Learned from Scaling Enterprise SaaS Teams by Mark Josephson (CEO, Bitly)

Next up we welcomed Mark, who presented his three lessons around finding the right talent, efficiently focusing on your plan, and understanding the math behind your business in order to scale. Within this, he nailed it in terms of his advice on how to tackle all three.

1. Regarding talent, you simply need to find folks who allow you to let go, and sleep at night. Tactically speaking, you need to hire people who know how to do the job, and this means that they understand how to do the job at the stage of your business you’re currently at, or about to head into. In other words, don’t assume the VP of Sales at XYZ IPO’d tech company is automatically a good VP of Sales at ABC seed-stage tech company in the same vertical. Mark also highlighted that an enterprise AE is very different than someone with great sales skills in selling a product at a vastly different price point.

2. Focusing on your plan seems simple enough, right? Well there are a lot of distractions that can come up, but Mark encourages us to empower our sales ops teams (one of the main drivers of sales team focus) to lead the effort of what to focus on. Mark also discussed the idea that “everyone in the company is in sales” and therefore it’s important for sales leaders to create allies in their marketing, product, and other leadership counterparts in order to work together.

3. Finally, Mark touched on understanding the math of your business, as this can be the divider between seemingly good ideas, and efficient ideas in reality. For example, Mark talked about adding salespeople on a whim, and why that sometimes doesn’t increase revenue in a linear fashion, but if we could instead reduce sales ramp up time by half, and increase ACV by 20% because we’ve hired experienced enterprise AEs, then we start to achieve economies of scale that work. A precursor to our Sales Velocity fireside chat later in the day.

Excellent wisdom, Mark!

Strategies for Expanding Into New Geographies by James Allgrove (Head of Growth, US East Coast at Stripe)

We couldn’t think of a better person to tackle this talk at the Sales Summit, as James headed up Stripe’s UK Operations, and grew their team from 3 to 25 people there before focusing on growth for the East Coast. James started by outlining some factors your team should study before opening offices in a new geography: regulation & politics, competition, language & culture, organization (from a communication standpoint), investment cost, timezone considerations. Study all of these, be at peace with the challenges you may face, and then execute! James also blessed us with this wonderful decision-making chart to use when making strategic decisions across geographies:

In the top right corner, he mentioned things like naming products for new geographies or segments. It’s hard to change names of products frequently, so move cautiously. On the opposite end of the spectrum, he mentioned creating personalized collateral in different languages with the loose advice of: go for it! If it’s slightly wrong or needs to be adjusted for the culture, that’s easier to do on the fly than recreating products or websites. Some final advice from James: start by hiring generalists in a geography, and move towards role specialization as successful proof points within the region roll in.

Thanks and onward, James!

Evolving from Founder-Driven Sales to Hiring Your First Sales Team (Panel, See Below)

Alex Adamson, Director of Talent at Bowery Capital hosted a wonderful panel at the Sales Summit on a topic she knows best – hiring your first sales team, and retiring your role of being the only seller, as a founder. She was joined by Jordan Wan (founder of CloserIQ), Jennifer Etherton (Head of Sales at Klara) and Rachel Kaplowitz (CEO & Founder of Honey) who have all tackled this same challenge from different angles.

Collectively, their advice was the following:

1. Your sales team is going to evolve over time. The sellers that you need in your early years are very different than the folks that you will hire down the road once you have product-market-fit and data about your sales processes.

2. Hire early sellers who are bought in on the company vision and make sure that they feel and know that they’re an influential part of the founding team. They’re going to be going through a lot of the ups and downs during the “tinkering stage,” and will be asked to do more than just hit their quota, so be able to motivate them with things that aren’t just compensation such as leadership/mentorship opportunities.

3. You will always be selling as a founder, but hire people that you trust and don’t micromanage them when they’re on the team. Don’t put yourself in a position to compete with them on deals, and make it clear that you trust them to do what you hired them to do: sell!

Thanks Alex, Jordan, Jennifer, and Rachel!

Building an Enterprise Sales Playbook within a Freemium SaaS Company by Julie Maresca (Head of Enterprise Sales, East at Slack)

Julie joined the Sales Summit to talk about the journey of Slack from simply being a freemium machine to, well, being that and an enterprise sales machine! Many core tenets stuck out in Julie’s talk as to how Slack (and others) can take a freemium product and build an enterprise playbook around it:

1. Consistent measuring of customer satisfaction (via NPS scores, CSAT and more) is key as you empower a newly hired accounts team to understand where they can and should upsell freemium or lower-paying customers.

2. Rinse and repeat in segmenting your market! You should create an initial hypothesis around what signals your freemium customers need to show before they go from free (and automated) to paid (and engaging with human account managers/sellers). You should continue to develop this hypothesis to segment your paid customers further so that you can understand how to build different “sales muscles” for different segments.

3. Your first sales hires in addressing this strategy should be “general athletes”, and specialize over time into “starting pitchers”, “closers”, etc. By the way, Slack started with an accounts team focused on existing customers and scaling the management of those into higher paid plans, before hiring these sales general athletes almost a year later.

4. Through all of this, customer support is essential, and rewarding your customers in fun and unique ways creates loyalty that keeps the overall engine going!

Thanks for taking us through the Slack journey, Julie!

10 Data-Driven Ways to Increase Pipeline by Jeremey Donovan (SVP Sales Strategy & GM NYC at SalesLoft)

If you’d like data on how to create near-perfect and thoughtful sales messaging and cadences, look no further. Jeremey and the SalesLoft team wowed the Sales Summit with their impressive level of expertise here, and their advice was effective, fun, and engaging. Some of our favorite key data points below from Jeremey and co:

1. When it comes to responding to inbound, speed is key, but don’t be too fast! For best results, respond within the hour. Responding within 5 mins is actually less effective in terms of the results. Perhaps it feels less personal and contrived to respond this quickly.

2. 80% of the top 100 cadences SalesLoft looked at (across a sample size of 3MM+) started with both a phone call and email on Day 1 of the cadence.

3. Personalizing up to 20% of your emails, results in a 2x reply rate. Personalizing more than this though is actually a waste of time due to diminishing returns against the time and effort it takes to do this.

4. Subject lines matter! Here are the most effective words to use in a subject line (with reply rates relative to the sample average):5. Video in the email body of a sales message increases reply rates by 25%! That said, video is best in follow up emails, not your initial note to a prospect.

6. And finally, despite using many in this post, bullets in emails are bad! Emails with bullets have a 19% lower reply rate.

We could have asked Jeremey questions until the lights went off at the Sales Summit. Great tips, and thanks again for sharing them with us!

Building a Culture Around Sales Velocity (Fireside Chat, See Below)

Finally, Andrew Oddo (Director of Growth at Bowery) and Matt Roy (Head of BD & Partnerships at InsightSquared) rounded out the Sales Summit by discussing the idea of sales velocity. Not sure what sales velocity is? Andrew kicked off by asking Matt for his definition of sales velocity, and he basically outlined the following equation, which helps you to gauge pipeline momentum, and how much revenue you stand to close for a given time period.

Additionally, Matt highlighted, with obvious wisdom of experience here, that you can use this as the vehicle for great 1:1s with your reportees, by starting the conversation asking “Why do YOU think you’re struggling to achieve your quota or could be doing better?”. After that, you can dig into the mechanics of how sales velocity works with your team members, and often they’ll realize things like the fact that they don’t need more leads, but they may need to maintain better task management discipline to keep deal cycles tight, or acquire better negotiation skills to increase close rates.

Finally, Matt suggested that it’s good to measure these four metrics for both the team as a whole and individual team members. This will truly help to embed it in your culture, and also empower individual reps to understand where they excel against the team, where they fall short, and what they can do to own and improve their personal sales operation. Love these strategies, Matt!

In conclusion, we learned a ton, and would like to offer a special thanks to all our Sales Summit speakers, and especially our sponsors CloserIQ, InsightSquared, SalesLoft, and Buhler Duggal & Henry. Additional thanks Rise New York for hosting and CredPR for helping us organize the event! If you’d like to see the full set of the slides, head here. See you at next year’s Sales Summit, and good luck kicking off 2019!